Imidazole compounds having fungicidal activity

Abstract

There are disclosed an imidazole derivative represented by the formula: ##STR1## wherein R 1 and R 2 each represent a hydrogen atom or a C 1-4 alkyl group, provided that both of R 1 and R 2 do not represent an alkyl group at the same time, or may be combined with each other to form a group ═CHR 4 , where R 4 represents a C 1-4 alkyl group; when R 1 and R 2 each represent a hydrogen atom or a C 1-4 alkyl group, R 3 represents a C 1-12 alkyl group, a C 1-12 alkenyl group, a phenylalkyl group, a phenylalkenyl group, a phenoxyalkyl group or a phenoxyalkenyl group; and when R 1 and R 2 represent a group ═CHR 4 , R 3 represents a C 4-10 alkyl group, a C 4-10 alkenyl group or a phenylalkyl group; a method for preparing the same and a fungicide containing the same as an active ingredient and a fungicidally acceptable carrier.

We claim: 
     
       1. An imidazole compound of the formula: wherein R 1  and R 2  each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, provided that both of R 1  and R 2  do not represent an alkyl group at the same time, or together form a group ═CHR 4 , where R 4  represents an alkyl group having 1 to 4 carbon atoms; when R 1  and R 2  each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 3  represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 1 to 12 carbon atoms, a phenyl-C 1-12  -alkyl group, a phenyl-C 3-12  -alkenyl group, a phenoxy-C 2-12  -alkyl group or a phenoxy-C 3-12  -alkenyl group, and the phenyl rings of the phenyl-C 1-12  -alkyl, phenyl-C 3-12  -alkenyl, phenoxy-C 2-12  -alkyl and phenoxy-C 3-12  -alkenyl groups are optionally substituted with at least one substituent selected from a halogen atom, a C 1-12  -alkyl group, a C 1-12  -alkoxy group, a C 3-12  -alkenyloxy group and a phenoxy group; and when R 1  and R 2  together form the group ═CHR 4 , R 3  represents an alkyl group having 4 to 10 carbon atoms, an alkenyl group having 4 to 10 carbon atoms or a phenyl-C 1-12  -alkyl group having a phenyl ring optionally substituted with at least one substituent selected from a halogen atom, a C 1-12  -alkyl group, a C 1-12  -alkoxy group, a C 3-12  -alkenyloxy group and a phenoxy group.   
     
     
       2. The imidazole compound according to claim 1, wherein R 1  is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 2  is a hydrogen atom and R 3  is an alkyl group having 4 to 10 carbon atoms, a phenylalkyl group containing a straight C 1-5  alkyl group, a phenylalkenyl group containing a straight C 3-6  alkenyl group, a phenoxylalkyl group containing a straight or branched C 2-5  alkyl group or a phenoxylalkenyl group containing a straight or branched C 3-5  alkenyl group. 
     
     
       3. The imidazole compound according to claim 1, wherein R 1  is a hydrogen atom, a methyl group, an ethyl group or a propyl group and R 3  is an n-pentyl group, an n-hexyl group, an n-octyl group, an n-decyl group, an n-hexenyl group, an unsubstituted benzyl group, or a benzyl group substituted with at least one substituent selected from a halogen atom, a C 1-12  -alkyl group, a C 1-12  -alkoxy group, a C 3-12  -alkenyloxy group and a phenoxy group. 
     
     
       4. The imidazole compound according to claim 1, wherein R 1  and R 2  together form the group ═CHR 4 , and R 3  is a straight or branched alkyl group having 4 to 10 carbon atoms, a straight or branched alkenyl group having 4 to 10 carbon atoms, or a phenyl-C 1-12  -alkyl group substituted with a straight or branched alkyl group having 1 to 12 carbon atoms. 
     
     
       5. The imidazole compound according to claim 4, wherein R 4  is a methyl group and R 3  is a straight alkenyl group having 4 to 10 carbon atoms or a phenyl-C 1-12  -alkyl group substituted with a straight alkyl group having 1 to 4 carbon atoms. 
     
     
       6. A fungicide composition comprising a fungicidally effective amount of a compound of the formula (I): ##STR45## wherein R 1  and R 2  each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, provided that both of R 1  and R 2  do not represent an alkyl group at the same time, or together form a group ═CHR 4 , where R 4  represents an alkyl group having 1 to 4 carbon atoms; when R 1  and R 2  each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 3  represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 1 to 12 carbon atoms, a phenyl-C 1-12  -alkyl group, a phenyl-C 3-12  -alkenyl group, a phenoxy-C 2-12  -alkyl group or a phenoxy-C 3-12  -alkenyl group, and the phenyl rings of the phenyl-C 1-12  -alkyl, phenyl-C 3-12  -alkenyl, phenoxy-C 2-12  -alkyl and phenoxy-C 3-12  -alkenyl groups are optionally substituted with at least one substituent selected from a halogen atom, a C 1-12  -alkyl group, a C 1-12  -alkoxy group, a C 3-12  -alkenyloxy group and a phenoxy group; and when R 1  and R 2  together form the group ═CHR 4 , R 3  represents an alkyl group having 4 to 10 carbon atoms, an alkenyl group having 4 to 10 carbon atoms or a phenyl-C 1-12  -alkyl group having a phenyl ring optionally substituted with at least one substituent selected from a halogen atom, a C 1-12  -alkyl group, a C 1-12  -alkoxy group, a C 3-12  -alkenyloxy group and a phenoxy group; according to claim 1 as the active ingredient, and a fungicidally acceptable carrier.   
     
     
       7. The fungicide composition according to claim 6, wherein R 1  is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 2  is a hydrogen atom and R 3  is an alkyl group having 5 to 10 carbon atoms, a straight alkenyl group having 4 to 10 carbon atoms, a phenylalkyl group containing a straight C 1-5  alkyl group, a phenylalkenyl group containing a straight C 3-6  alkenyl group, a phenoxylalkyl group containing a straight or branched C 2-5  alkyl group or a phenoxylalkenyl group containing a straight or branched C 3-5  alkenyl group. 
     
     
       8. The fungicide composition according to claim 6, wherein R 1  is a hydrogen atom, a methyl group, an ethyl group or a propyl group and R 3  is an p-pentyl group, an n-hexyl group, an n-octyl group, an n-decyl group, an n-hexenyl group, an unsubstituted benzyl group, or a benzyl group substituted with at least one substituent selected from a halogen atom, a C 1-12  -alkyl group, a C 1-12  -alkoxy group, a C 3-12  -alkenyloxy group and a phenoxy group. 
     
     
       9. The fungicide composition according to claim 6, wherein R 1  and R 2  together form the group ═CHR 4 , and R 3  is a straight or branched alkyl group having 4 to 10 carbon atoms, a straight or branched alkenyl group having 4 to 10 carbon atoms, or a phenyl-C 1-12  -alkyl group substituted with a straight or branched alkyl group having 1 to 12 carbon atoms. 
     
     
       10. The fungicide composition according to claim 9, wherein R 4  is a methyl group and R 3  is a straight alkenyl group having 4 to 10 carbon atoms or a phenyl-C 1-12  -alkyl group substituted with a straight alkyl group having 1 to 4 carbon atoms.